The Boston baseball club’s chief IT executive explains what distinguishes high-performing teams and how IT leaders can transform strategic relationships and pragmatic innovation into a winning IT culture. In his capacity as SVP and CTO of the Boston Red Sox, Brian Shield oversees the strategic direction of technology, fan engagement, daily IT operations, and cybersecurity for the benefit of the team, their supporters, and Fenway Sports Management. Throughout his career, Shield has worked for a number of national bellwether companies and industries, including FTD and The Weather Channel.
For a recent Tech Whisperers podcast episode, Shield and I had a seat inside the New England Sports Network Studios (NESN). We covered a wide range of subjects in that extensive talk, including his leadership playbook, the components of a winning data strategy, and the importance of pushing yourself as a leader. Shield then spoke for a little while further about some of the qualities of exceptional leaders and how to assemble a top-notch IT team. This Q&A has been condensed for length and clarity.
Brian Shield: Developing elite teams is a critical component for every successful CIO or CTO. I’ve always believed that successful sports organizations might teach traditional businesses and IT organizations a lot about how to build teams and develop players. Developing the appropriate talent is the first step for any successful team, whether they play IT or baseball. Like the finest IT teams, winning baseball teams have clearly defined roles, very effective leadership, and a deliberate staff development program. In baseball, you begin with a young, talented farm system. There are athletes with specialized abilities, such as defensive talent, relief pitchers, and base stealers. Your best players are in your starting lineup. Ideally, you have a manager, a coaching staff, and a couple All-Stars.
You might add free agents to complete your squad to add depth to your team. A development plan specifically tailored to each player is essential to their success. Complete transparency is used to identify areas of strength, weakness, and growth, supported by measurable results. These strategies are essential to a player’s success but, more significantly, to their capacity to change course when their rivals do.
IT teams that succeed are a lot like each other. Successful CIOs should always be on the lookout for fresh talent. Their objective is to hire competent interns and early-career resources in order to cultivate emerging talent. They have a channel, similar to baseball scouting organizations, into schools and universities. It is assumed that these rookies will pick up skills from both the veterans and their instructors or managers. IT teams hire specialists with specific subject knowledge and add their own “free agents,” or consultants, to the mix. Your starting lineup consists of seasoned leaders. Your all-stars are the greatest of the best. The CIO and your leadership team are at the top of the pyramid.
When compared to prosperous ball clubs, most IT teams fall short in terms of their dedication to worker development. Too frequently, we view professional development as a year-end evaluation of our strengths and shortcomings, with little willingness to be honest about our shortcomings and less dedication to a strategy that would help us improve. A high-performing squad with a variety of complementing talents that can develop, grow, and mature to help the team win far into the future will result from well-executed growth.
What kind of perspective do you use when hiring new team members?
This is an excellent query, especially given how quickly the world is changing these days. We search for talented athletes more than in the past. I don’t say that because of the type of business we operate in; rather, we search for resources who possess the necessary abilities for the position and—more importantly—who have a strong desire to learn and develop.
Which viewpoint do you apply when selecting new team members?
This is a really good question, especially considering how quickly things are changing in the modern world. More than in the past, we look for gifted athletes. I don’t say that to disparage the kind of business we conduct; rather, we look for people who are highly motivated to grow and learn and who have the skills required for the role.
Instead of being suppliers, great leaders are renowned for having strategic partners. What are the advantages of investing in and cultivating these relationships? It’s crucial to understand the distinction between vendors and strategic partners. I believe that merchants all too frequently consider themselves to be merely service providers. We actively search for a strategic partner, which I define as someone who is not only pitching a service or a product but also considering our long-term needs. This partner may be on another sales call for an entirely different business, but something will always occur to them that would be a perfect fit for the Red Sox. Someone who consistently puts us first